The 30 most painful NBA Draft pass-ups since 2000

Greg Oden #20 of the Miami Heat on the bench during an NBA game (Photo by Christian Petersen/Getty Images)
Greg Oden #20 of the Miami Heat on the bench during an NBA game (Photo by Christian Petersen/Getty Images) /
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NBA Draft Mistake #24: Philadelphia drafting Ben Simmons over Jaylen Brown.

Prior to the 2016 NBA Draft, 6’11 point-forward Ben Simmons appeared to be a no-brainer choice for the Philadelphia 76ers with the number one pick. He mostly lived up to the hype, at least initially. He was a two-time all-star, made the all-NBA second team in 2019, and was one of the better defensive players in the league.

That all changed in the Sixers 2021 semifinal series against the Atlanta Hawks, where Simmons imploded under pressure, including passing up a game-tying layup in Game 7.

After the series, then Sixers coach Doc Rivers criticized Simmons, leading to him demanding a trade that summer or threatening to sit out. Philadelphia wouldn’t give in, however, and he sat out for most of the season until he was traded to the Brooklyn Nets in a deal for superstar James Harden.

While getting Harden helped salvage the situation, Harden appears likely to leave in free agency, and the Sixers’ season was ended in part by a player that they passed on drafting. Jaylen Brown was selected third overall in the same draft and had a career year this season, far exceeding even Simmons’ best year with the Sixers. The decision not to draft Brown could very well hurt Philadelphia for the next several seasons.

After all, Boston and Philadelphia play in the same conference and have already played each other three times in the postseason since the 2016 Draft, with the Celtics going 3-0. Passing over Brown, in combination with a soon-to-be-discussed decision, both limited the Sixers’ ceiling and helped their archrival land two stars. Not great.